2-Bromo-1,1-dimethoxyethane → HCID 57428870, compound

HRID 2267443Notes

Reaction equation

HRID 2267443 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[C:6]([C:14](=[S:16])[NH2:15])=[CH:5][N:4]=1.CO[CH:19](OC)[CH2:20]Br>C(O)C.Cl>[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[C:6]([C:14]2[S:16][CH:19]=[CH:20][N:15]=2)=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 816722-Bromo-1,1-dimethoxyethane2×HCID 57428869HCID 57428869, compound

Product 1

HCID 57428870HCID 57428870, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

2-(Methylthio)-4-(thiophen-2-yl)pyrimidine-5-carbothioamide (0.3 g, 1.12 mmol) suspended in ethanol (2 mL) was treated with bromoacetaldehyde dimethylacetal (0.158 mL, 1.34 mmol). The reaction was stirred at reflux overnight. No product formation was observed by thin layer chromatography in 20% ethyl acetate/hexanes. Another equivalent of bromoacetaldehyde dimethylacetal was added to the reaction in addition to a few drops of concentrated hydrochloric acid and the reaction kept at reflux for another 3 h. The reaction was cooled down to room temperature and the volatiles removed in vacuo. A solution of saturated sodium bicarbonate was added to the residue, which was extracted with dichloromethane. The organic layer was dried with sodium sulfate and purified by flash chromatography using a gradient of 20 to 60% of ethyl acetate in hexanes. The product was obtained as a brown solid (0.18 g). MS (M+H)+ 292.

Workup

  1. temperatureat reflux overnight
  2. temperatureat reflux for another 3 h
  3. customthe volatiles removed in vacuo
  4. additionA solution of saturated sodium bicarbonate was added to the residue, which
  5. extractionwas extracted with dichloromethane
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-f789f8a0d9694fd3a6324e4559c10dc9
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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